Syntheses and Application of Aminated Benzimidazole Derivatives in Transfer Hydrogenation Reaction of Ketones

doi:10.6023/cjoc201203013

Chin. J. Org. Chem. ›› 2012, Vol. 32 ›› Issue (07): 1247-1254.DOI: 10.6023/cjoc201203013 Previous Articles Next Articles

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氨基取代的苯并咪唑衍生物的合成及在酮的氢转移反应中的应用

段凯, 李小娜, 李云庆, 王家喜

河北工业大学化工学院,天津 300130

收稿日期:2012-03-30 修回日期:2012-05-07 发布日期:2012-05-11
通讯作者: 王家喜 E-mail:jwang252004@126.com
基金资助:
河北省自然科学基金(No. B2011202087 )资助项目.

Syntheses and Application of Aminated Benzimidazole Derivatives in Transfer Hydrogenation Reaction of Ketones

Duan Kai, Li Xiaona, Li Yunqing, Wang Jiaxi

School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received:2012-03-30 Revised:2012-05-07 Published:2012-05-11
Supported by:
Project supported by the Natural Science Foundation of Hebei province of China (No. B2011202087)

A series of α-amino-benzimidazole derivatives (1~5) were synthesized by reaction of α-amino acid with o-phenylenediamine under microwave irradiation. 1-(1H-benzo[d]imidazol-2-yl)ethanamine 1 reacted with bromobutane forming mono-butyl, dibutyl and tributyl substituted benzimidazole (1a~1d); and the N-alkylated derivatives (1i~1g) were synthesized by protection of amine group by Boc and then N-alkylation. The catalytic capability of the catalyst generated in situ from Ru (Ⅱ) compound and obtained benzimidazole derivatives were evaluated in the transfer hydrogenation of ketone using iso-PrOH as hydrogen donor and solvent. The results revealed that catalyst generated in situ from RuCl₂(PPh₃)₃ and ligands had moderate to high activity. The catalyst system with α-amino-benzimidazole derivative containing NH₂ group is the most active and the highest TOF was up to 40200 h^-1.

Key words: amino acid, benzimidazole, N-alkylation, microwave, Ru(Ⅱ) complex, ketone, transfer hydrogenation

Cite this article

Duan Kai, Li Xiaona, Li Yunqing, Wang Jiaxi. Syntheses and Application of Aminated Benzimidazole Derivatives in Transfer Hydrogenation Reaction of Ketones[J]. Chin. J. Org. Chem., 2012, 32(07): 1247-1254.

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氨基取代的苯并咪唑衍生物的合成及在酮的氢转移反应中的应用

Syntheses and Application of Aminated Benzimidazole Derivatives in Transfer Hydrogenation Reaction of Ketones

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